Wainwright is a tricky right winger who can be very creative. Neil started his football at Welsh side Wrexham in the summer of 1996. In two years there he made roughly 12 appearances before Weirsiders Sunderland came in with a bid of £100,000 to take him up North. Despite other clubs such as Newcastle, Derby and Coventry he decided that Sunderland was for him.

Wainwright had a tough time at Sunderland and between 1998 and 2001 he made only 3 first team appearances for the Black Cats. Sunderland decided to put the winger on the loan list to let him gain some first team football experience. In February of 2000 Darlington came in and loaned him for a month. The club was of course chasing promotion that season. He made his debut in a Quakers shirt against Peterborough. He ran Peterborough ragged on the right wing and scored as well. Neil went on to make a further 15 appearances and scored a further 3 goals. His initial month loan spell was increased till the end of the season. Darlington's promotion bid faltered and in the end we had to go to the play-offs. By this point Neil's loan spell had finished and Darlington could no longer loan him out due to league rules. He returned to Sunderland.

The next season Neil joined Halifax Town on loan. He made 16 appearances for the Shaymen, one of them included a return trip to Darlington were he crossed for one of the goals. Darlington kept a close eye on the player but were not willing to splash the cash. Before the start of the 2001/02 season Darlington were linked with Wainwright. There was a lengthy on off saga but eventually he signed for Darlington before the first home game of the season against Kidderminster.

When David Hodgson returned during the 2003/04 season Wainwright was pressed into service as a forward and while finding goals hard to come by worked his socks off in the new role and put in some die hard performances which fans appreciated. Wainwright has always been a hard working player but the return of Hodgson really helped him. Normally the last off the pitch at away games and always applauds the people who make the long away games.